Tetrahydrofuran → 4'-bromo-N-methyl-2'-aminobenzanilide

HRID 420470Notes

Reaction equation

HRID 420470 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([N:6]([CH3:15])[C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([N+:18]([O-])=O)[CH:3]=1.O1CCCC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.CO>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([N:6]([CH3:15])[C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([NH2:18])[CH:3]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 230940784'-bromo-N-methyl-2'-nitrobenzanilide

Product 1

HCID 230940734'-bromo-N-methyl-2'-aminobenzanilideYield 91.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Dissolving 9.5 g (28 mmol) of 4′-bromo-N-methyl-2′-nitro-benzanilide obtained in the above step (2) into 100 milliliter of tetrahydrofuran, and during agitation under the atmosphere of argon gas and at room temperature, a solution provided by mixing 25 g (0.14 mmol) of sodium hydrosulfite into 90 milliliter of water was added. Further, adding 10 milliliter of methanol, the resultant solution was stirred for 3 hours. Subsequently, adding 100 milliliter of ethyl acetate and then, a solution provided by mixing 12 g (0.14 mmol) of sodium hydrogen carbonate and 125 milliliter of water was further added. The resultant solution was stirred for 1 hour, followed by extracting with ethyl acetate. After removing water layer, an organic layer was washed with 10% K2CO3 aqueous solution and with saturated solution of sodium chloride, followed by drying with the use of magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure and 7.8 g of 4′-bromo-N-methyl-2′-amino-benzanilide was obtained as white solids (yield: 90%). The white solids were used in the next reaction as crude products.

Workup

  1. customduring agitation under the atmosphere of argon gas and at room temperature, a solution provided
  2. additionwas added
  3. customa solution provided
  4. additionwas further added
  5. extractionby extracting with ethyl acetate
  6. customAfter removing water layer
  7. washan organic layer was washed with 10% K2CO3 aqueous solution and with saturated solution of sodium chloride
  8. dry with materialby drying with the use of magnesium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-97284848dc48448b99ccbc4f7540e52a
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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